Hydrazine hydrate (1:1) → 3-Pyridinecarboxylic acid, 2-amino-4,6-bis(trifluoromethyl)-, hydrazide

HRID 1730650Notes

Reaction equation

HRID 1730650 reaction equation
[NH2:1][C:2]1[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:4](OCC)=[O:5].O.[NH2:22][NH2:23]>C(O)(C)C>[NH2:1][C:2]1[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:4]([NH:22][NH2:23])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12275047ETHYL 2-AMINO-4,6-BIS(TRIFLUOROMETHYL)NICOTINATE

Product 1

HCID 122750483-Pyridinecarboxylic acid, 2-amino-4,6-bis(trifluoromethyl)-, hydrazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-amino-4,6-di(trifluoromethyl)-nicotinate (2.55 g., 8.45 mmole), 85% hydrazine hydrate (5 ml.) and isopropanol (5 ml.) is stirred in an oil-bath at 110° C. for 3 hours. On cooling, the dark red solution deposits colorless crystals which are filtered off and washed with a little isopropanol. A second crop of solid is obtained by evaporation of the mother liquors giving a total yield of 1.45 g. (59.6%) of product, m.p. 240°- 243° C. (dec.). Upon recrystallization from isopropanol (25 ml.) there is obtained 1.05 g. (42.8%) of product, m.p. 244°-245° C. (dec.).

Workup

  1. temperatureOn cooling
  2. filtrationthe dark red solution deposits colorless crystals which are filtered off
  3. washwashed with a little isopropanol
  4. customA second crop of solid is obtained by evaporation of the mother liquors
  5. customgiving a total yield of 1.45 g
  6. customUpon recrystallization from isopropanol (25 ml.) there
  7. customis obtained 1.05 g

Sources & evidence

ORD record
ord-32edb6dc47ba4784a96160c9aaef7c1c
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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